NP-MRD: Showing NP-Card for (1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene (NP0157276)

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Record Information

Version

2.0

Created at

2022-09-02 14:37:25 UTC

Updated at

2022-09-02 14:37:25 UTC

NP-MRD ID

NP0157276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene

Description

CHEMBL509424 belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. (1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene is found in Acanthella pulcherrima, Axinella cannabina, Axinyssa ambrosia and Cadlina luteomarginata. Based on a literature review very few articles have been published on CHEMBL509424.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.1548    2.4905   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5633    1.4151    0.8595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7022    0.7289    1.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3494   -0.3566    0.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860   -1.3688    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -0.7240   -0.5718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1062   -0.3521   -1.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3052   -1.7759   -0.9480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0526   -1.6101   -0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5267   -0.1975   -0.6481 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9524   -0.0695   -0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1076   -0.3071    1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -0.9581   -0.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3606    1.3111   -0.4728 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4693    2.1997    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2170    3.4867    1.3528 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6050    0.7078    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170    0.4558    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4984    2.7505   -0.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3077    3.4483    0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1631    2.2312   -0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9764    1.9519    1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768    0.3211    2.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665    1.5195    1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680   -0.8755    1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8899    0.0477   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6930   -2.3064    0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7007   -1.5759    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6305   -0.7941   -2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1312   -0.7852   -1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610    0.7247   -1.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1524   -1.7380   -2.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7137   -2.8024   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0545   -1.8038    0.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395   -2.3086   -0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4536   -0.0459   -1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -0.4606    1.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7455   -1.2170    1.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6731    0.5249    1.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6497   -0.8823   -2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086   -2.0220   -0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9161   -0.5526   -0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0216    1.5745    0.5786 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  1  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 17  1  0
 17 18  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  2  0
 18  2  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  6
 17 43  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 13 42  1  0
M  END


  Mrv1652309022216372D          

 18 19  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   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
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 S   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  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
  6 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC[C@]2(C)CC[C@@H](C=C12)C(C)(C)N=C=S

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NS/c1-12-6-5-8-16(4)9-7-13(10-14(12)16)15(2,3)17-11-18/h10,12-13H,5-9H2,1-4H3/t12-,13-,16+/m0/s1

> <INCHI_KEY>
YZYZKKAHYRXPMB-HEHGZKQESA-N

> <FORMULA>
C16H25NS

> <MOLECULAR_WEIGHT>
263.44

> <EXACT_MASS>
263.170770983

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.179504724661008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aR,7S)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene

> <ALOGPS_LOGP>
6.13

> <JCHEM_LOGP>
5.062021370333333

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5954158806314704

> <JCHEM_POLAR_SURFACE_AREA>
12.36

> <JCHEM_REFRACTIVITY>
82.5018

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.95e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aR,7S)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.232  -4.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.772  -1.746   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       9.336  -3.850   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       9.336  -6.930   0.000  0.00  0.00           S+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   18                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   10   18                                                       
CONECT   18   17    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₅NS

Average Mass

263.4400 Da

Monoisotopic Mass

263.17077 Da

IUPAC Name

(1S,4aR,7S)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene

Traditional Name

(1S,4aR,7S)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalene

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC[C@]2(C)CC[C@@H](C=C12)C(C)(C)N=C=S

InChI Identifier

InChI=1S/C16H25NS/c1-12-6-5-8-16(4)9-7-13(10-14(12)16)15(2,3)17-11-18/h10,12-13H,5-9H2,1-4H3/t12-,13-,16+/m0/s1

InChI Key

YZYZKKAHYRXPMB-HEHGZKQESA-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
Acanthella pulcherrima	LOTUS Database	35616633
Axinella cannabina	LOTUS Database	35616633
Axinyssa ambrosia	LOTUS Database	35616633
Cadlina luteomarginata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Isothiocyanate
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
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	6.13	ALOGPS
logP	5.06	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-3.6	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	2	ChemAxon
Refractivity	82.5 m³·mol⁻¹	ChemAxon
Polarizability	31.18 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

8168527

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9992945

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene (NP0157276)

MOL for NP0157276 ((1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene)

3D MOL for NP0157276 ((1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene)

3D SDF for NP0157276 ((1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene)

3D-SDF for NP0157276 ((1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene)

PDB for NP0157276 ((1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene)

3D PDB for NP0157276 ((1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene)

SMILES for NP0157276 ((1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene)

INCHI for NP0157276 ((1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene)

Structure for NP0157276 ((1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene)

3D Structure for NP0157276 ((1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene)