NP-MRD: Showing NP-Card for n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride (NP0192095)

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Record Information

Version

2.0

Created at

2022-09-04 09:13:31 UTC

Updated at

2022-09-04 09:13:32 UTC

NP-MRD ID

NP0192095

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride

Description

CHEMBL516571 belongs to the class of organic compounds known as isocyanide dichlorides. These are organonitrogen compounds derived from isocyanide, with the general formula RN=C(Cl)Cl (R = organyl). n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride is found in Stylissa massa. Based on a literature review very few articles have been published on CHEMBL516571.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
   -1.7777    1.9853    1.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8003    0.8467    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2561    1.4926   -1.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033   -0.1464    0.7169 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3822    0.3105   -0.0198 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433   -1.5587    0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1028   -1.9681    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -1.0074   -0.4137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6223   -1.1257   -1.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896   -1.4577   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687   -0.3784   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4252   -0.7051   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4428    0.2831   -0.7283 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5674    0.2183   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9898   -1.1575    0.8179 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7180    1.5105   -0.3524 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9120    1.0406   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4855    1.3570   -0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3942    0.3377    0.1882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7090    1.9967    1.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6557    2.9622    0.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9431    1.8474    2.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9611    2.3394   -0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8617    0.8002   -1.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4251    1.9661   -1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9808   -0.0465    1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0700   -1.8442   -0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0557   -2.1985    1.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7435   -1.9105    1.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348   -3.0025   -0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2831   -0.3298   -2.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1579   -2.0769   -2.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7252   -1.2844   -2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3772   -2.2650   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885   -1.9611    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6883   -1.7385   -0.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6402    1.7087   -0.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9041    1.2041    1.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2557    2.3901   -0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    1.3033   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0295    0.2622    1.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  6
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 19  1  0
 19 18  1  0
 18 17  1  0
 17 11  1  0
 11 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 19  8  1  0
 10  8  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
  7 29  1  0
  7 30  1  0
  6 27  1  0
  6 28  1  0
  4 26  1  1
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 19 41  1  1
 18 39  1  0
 18 40  1  0
 17 37  1  0
 17 38  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
M  END


  Mrv1652309042211132D          

 19 20  0  0  1  0            999 V2000
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  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
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 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
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
  2 19  1  0  0  0  0
  8 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0192095

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@H](Cl)C(C)(C)[C@@H]1CC\C(C2)=C/N=C(Cl)Cl

> <INCHI_IDENTIFIER>
InChI=1S/C15H22Cl3N/c1-14(2)11-5-4-10(9-19-13(17)18)8-15(11,3)7-6-12(14)16/h9,11-12H,4-8H2,1-3H3/b10-9+/t11-,12-,15+/m0/s1

> <INCHI_KEY>
FWCLKTGCAXVCAJ-ZORBJXORSA-N

> <FORMULA>
C15H22Cl3N

> <MOLECULAR_WEIGHT>
322.7

> <EXACT_MASS>
321.0817828

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
33.881822965700565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{[(2E,4aR,6S,8aR)-6-chloro-5,5,8a-trimethyl-decahydronaphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride

> <JCHEM_LOGP>
5.568042738666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.0192300494765814

> <JCHEM_POLAR_SURFACE_AREA>
12.36

> <JCHEM_REFRACTIVITY>
84.37979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-{[(2E,4aR,6S,8aR)-6-chloro-5,5,8a-trimethyl-hexahydro-1H-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5 Cl   UNK     0       0.000  -3.080   0.000  0.00  0.00          Cl+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       9.336  -0.770   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      10.669  -3.080   0.000  0.00  0.00          Cl+0
HETATM   16 Cl   UNK     0       8.002  -3.080   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   19                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   19                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   11   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    2    8                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂Cl₃N

Average Mass

322.7000 Da

Monoisotopic Mass

321.08178 Da

IUPAC Name

N-{[(2E,4aR,6S,8aR)-6-chloro-5,5,8a-trimethyl-decahydronaphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride

Traditional Name

N-{[(2E,4aR,6S,8aR)-6-chloro-5,5,8a-trimethyl-hexahydro-1H-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H](Cl)C(C)(C)[C@@H]1CC\C(C2)=C/N=C(Cl)Cl

InChI Identifier

InChI=1S/C15H22Cl3N/c1-14(2)11-5-4-10(9-19-13(17)18)8-15(11,3)7-6-12(14)16/h9,11-12H,4-8H2,1-3H3/b10-9+/t11-,12-,15+/m0/s1

InChI Key

FWCLKTGCAXVCAJ-ZORBJXORSA-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
Stylissa massa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocyanide dichlorides. These are organonitrogen compounds derived from isocyanide, with the general formula RN=C(Cl)Cl (R = organyl).

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Isocyanide dichlorides

Direct Parent

Isocyanide dichlorides

Alternative Parents

Substituents

Isocyanide dichloride
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.57	ChemAxon
pKa (Strongest Basic)	2.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.38 m³·mol⁻¹	ChemAxon
Polarizability	33.88 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

24717211

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44584725

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride (NP0192095)

MOL for NP0192095 (n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride)

3D MOL for NP0192095 (n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride)

3D SDF for NP0192095 (n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride)

3D-SDF for NP0192095 (n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride)

PDB for NP0192095 (n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride)

3D PDB for NP0192095 (n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride)

SMILES for NP0192095 (n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride)

INCHI for NP0192095 (n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride)

Structure for NP0192095 (n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride)

3D Structure for NP0192095 (n-{[(2e,4ar,6s,8ar)-6-chloro-5,5,8a-trimethyl-hexahydro-1h-naphthalen-2-ylidene]methyl}-1-chloromethanecarbonimidoyl chloride)