NP-MRD: Showing NP-Card for (2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene (NP0209492)

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Record Information

Version

2.0

Created at

2022-09-05 06:55:29 UTC

Updated at

2022-09-05 06:55:29 UTC

NP-MRD ID

NP0209492

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene

Description

(+)-Agroclavine belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines. Based on a literature review very few articles have been published on (+)-Agroclavine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -3.2658   -2.3691   -0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -1.3786   -0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0060   -1.6060   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1579   -0.5529    0.5716 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2786   -0.6955    0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9047   -1.9249    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2650   -1.9510   -0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0361   -0.8033   -0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4234    0.4389    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8301    1.7188    0.0219 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7516    2.5004    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6293    1.7162    0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0659    0.4207    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1924    1.9287    0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6109    0.7780    0.0202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9973    1.0347    0.2442 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6540    1.6812   -0.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7754   -0.1058    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160   -3.1624    0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8543   -2.7895   -1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2144   -1.8301   -0.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535   -2.5256   -0.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3127   -0.6131    1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2871   -2.7946    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762   -2.8989   -0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1035   -0.8388   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8001    2.0438   -0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232    3.5798    0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1212    2.8373    0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0884    2.0848    1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4221    0.7418   -1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593    0.9590   -1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116    2.5817   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6510    2.0299   -0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7475   -0.2903    1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8309    0.0547    0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  1  0
 18  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4 15  1  0
 15 14  1  0
 14 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5 13  2  0
 15 16  1  0
 13 12  1  0
  5  4  1  0
 13  9  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  1
 15 31  1  6
 14 29  1  0
 14 30  1  0
 11 28  1  0
 10 27  1  0
  8 26  1  0
  7 25  1  0
  6 24  1  0
M  END


  Mrv1652309052208552D          

 18 21  0  0  1  0            999 V2000
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  1  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  5 13  2  0  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209492

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC(C)=C[C@@H]2[C@@H]1CC1=CNC3=CC=CC2=C13

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,13,15,17H,7,9H2,1-2H3/t13-,15-/m0/s1

> <INCHI_KEY>
XJOOMMHNYOJWCZ-ZFWWWQNUSA-N

> <FORMULA>
C16H18N2

> <MOLECULAR_WEIGHT>
238.334

> <EXACT_MASS>
238.146998588

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.111063079842822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,7S)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),3,9,12,14-pentaene

> <JCHEM_LOGP>
2.775077040666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.04669835575154

> <JCHEM_PKA_STRONGEST_BASIC>
8.403408694833802

> <JCHEM_POLAR_SURFACE_AREA>
19.03

> <JCHEM_REFRACTIVITY>
76.0076

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,7S)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),3,9,12,14-pentaene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    5    9                                                  
CONECT   14   12   15                                                       
CONECT   15   14    4   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈N₂

Average Mass

238.3340 Da

Monoisotopic Mass

238.14700 Da

IUPAC Name

(2S,7S)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),3,9,12,14-pentaene

Traditional Name

(2S,7S)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),3,9,12,14-pentaene

CAS Registry Number

Not Available

SMILES

CN1CC(C)=C[C@@H]2[C@@H]1CC1=CNC3=CC=CC2=C13

InChI Identifier

InChI=1S/C16H18N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,13,15,17H,7,9H2,1-2H3/t13-,15-/m0/s1

InChI Key

XJOOMMHNYOJWCZ-ZFWWWQNUSA-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 clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Clavines and derivatives

Direct Parent

Clavines and derivatives

Alternative Parents

Substituents

Clavine skeleton
Benzoquinoline
Pyrroloquinoline
3-alkylindole
Quinoline
Isoindole or derivatives
Indole or derivatives
Indole
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
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	2.78	ChemAxon
pKa (Strongest Acidic)	17.05	ChemAxon
pKa (Strongest Basic)	8.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	19.03 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	76.01 m³·mol⁻¹	ChemAxon
Polarizability	28.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

933737

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene (NP0209492)

MOL for NP0209492 ((2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene)

3D MOL for NP0209492 ((2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene)

3D SDF for NP0209492 ((2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene)

3D-SDF for NP0209492 ((2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene)

PDB for NP0209492 ((2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene)

3D PDB for NP0209492 ((2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene)

SMILES for NP0209492 ((2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene)

INCHI for NP0209492 ((2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene)

Structure for NP0209492 ((2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene)

3D Structure for NP0209492 ((2s,7s)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),3,9,12,14-pentaene)