NP-MRD: Showing NP-Card for (-)-Isocomene (NP0064782)

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Record Information

Version

2.0

Created at

2022-04-28 09:04:04 UTC

Updated at

2022-04-28 09:04:04 UTC

NP-MRD ID

NP0064782

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Isocomene

Description

(-)-Isocomene belongs to the class of organic compounds known as angular triquinanes. These are triquinane with a structure based on a [6.3.0.0^1,5] Undecane carbon skeleton. Thus, (-)-isocomene is considered to be an isoprenoid. (-)-Isocomene is found in Berkheya radula, Callilepis salicifolia, Chamomilla recutina, Isocoma wrightii, Leoniopadium alpinum, Leontopodium alpinum, Mikania goyazensis, Morithamnus crassus, Porophyllum angustissimum, Schistostephium crataegifolium, Silphium perfoliatum and Synotis alata. Based on a literature review very few articles have been published on (-)-isocomene.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.0000    3.2418    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2555    1.9531    0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0570    1.7651   -0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909    0.3221   -0.2399 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8491    0.0565   -1.6245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4791    0.0075    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8513   -1.0672    1.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892   -0.6046    1.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549   -0.3670    0.1891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2020   -1.5983   -0.5631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8921   -2.6338    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -1.2074   -1.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458    0.2942   -1.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9279    0.6370   -0.0895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1028    0.5211    0.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4762    3.2821    1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7265    3.3845   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2610    4.0573    0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609    2.5949   -0.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2334   -0.6063   -2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8694   -0.4163   -1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0381    1.0347   -2.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3981   -0.3451    0.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216    0.8703    1.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9497   -2.0373    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2732   -1.0958    2.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3699    0.3479    2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2059   -1.3993    2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829   -2.1297   -0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1855   -3.1677    0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902   -3.3830   -0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6992   -2.1716    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250   -1.6273   -1.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379   -1.5434   -2.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7243    0.7810   -2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4046    0.6166   -1.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5335    1.5498    0.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9243   -0.0795    0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459    0.1632    1.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  9  8  1  1
  9 10  1  0
  9 14  1  0
  9  4  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 10 29  1  6
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  5 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
M  END

  Mrv1652304282211042D          

 15 17  0  0  1  0            999 V2000
   -0.1956   -0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506   -0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -1.3692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8843   -0.8843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6294   -0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5517   -1.3692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2968   -2.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718   -2.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7817   -2.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192   -0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9642   -0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1392   -0.0997    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6543    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192   -1.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506   -1.8541    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  1  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  1  0  0  0
  6 14  1  1  0  0  0
  3 15  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0064782

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@]2(C)C(C)=C[C@@]3(C)CCC[C@@]123

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11-6-9-14(4)12(2)10-13(3)7-5-8-15(11,13)14/h10-11H,5-9H2,1-4H3/t11-,13+,14+,15-/m0/s1

> <INCHI_KEY>
SAOJPWFHRMUCFN-MYPMTAMASA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.37507466048016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,8R)-2,5,6,8-tetramethyltricyclo[6.3.0.0^{1,5}]undec-6-ene

> <ALOGPS_LOGP>
5.87

> <JCHEM_LOGP>
4.11418621

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
65.62089999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,8R)-2,5,6,8-tetramethyltricyclo[6.3.0.0^{1,5}]undec-6-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.365  -0.186   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.841  -1.651   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.405  -2.556   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.651  -1.651   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.175  -0.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.897  -2.556   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.421  -4.021   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.881  -4.021   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.326  -5.266   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.142  -1.651   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.667  -0.186   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.127  -0.186   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.221   1.060   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.142  -3.461   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.841  -3.461   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8   15                                             
CONECT    4    3    5    6   12                                             
CONECT    5    4    1                                                       
CONECT    6    4    7   10   14                                             
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    4   13                                                  
CONECT   13   12                                                            
CONECT   14    6                                                            
CONECT   15    3                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1S,2S,5R,8R)-2,5,6,8-tetramethyltricyclo[6.3.0.0^{1,5}]undec-6-ene

Traditional Name

(1S,2S,5R,8R)-2,5,6,8-tetramethyltricyclo[6.3.0.0^{1,5}]undec-6-ene

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@]2(C)C(C)=C[C@@]3(C)CCC[C@@]123

InChI Identifier

InChI=1S/C15H24/c1-11-6-9-14(4)12(2)10-13(3)7-5-8-15(11,13)14/h10-11H,5-9H2,1-4H3/t11-,13+,14+,15-/m0/s1

InChI Key

SAOJPWFHRMUCFN-MYPMTAMASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Berkheya radula	Plant	KNApSAcK
Callilepis salicifolia	LOTUS Database	35616633
Chamomilla recutina	Plant	KNApSAcK
Isocoma wrightii	Plant	KNApSAcK
Leoniopadium alpinum	-	KNApSAcK
Leontopodium alpinum	Plant	KNApSAcK
Mikania goyazensis	LOTUS Database	35616633
Morithamnus crassus	LOTUS Database	35616633
Porophyllum angustissimum	LOTUS Database	35616633
Schistostephium crataegifolium	LOTUS Database	35616633
Silphium perfoliatum	LOTUS Database	35616633
Synotis alata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular triquinanes. These are triquinane with a structure based on a [6.3.0.0^1,5] Undecane carbon skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Angular triquinanes

Alternative Parents

Substituents

Angular triquinane sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Isocomane sesquiterpenoids (LMPR0103760002 )

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	5.87	ALOGPS
logP	4.11	ChemAxon
logS	-5.1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.62 m³·mol⁻¹	ChemAxon
Polarizability	25.38 Å³	ChemAxon
Number of Rings	3	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

C00021828

Chemspider ID

9206122

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11030948

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Isocomene (NP0064782)

MOL for NP0064782 ((-)-Isocomene)

3D MOL for NP0064782 ((-)-Isocomene)

3D SDF for NP0064782 ((-)-Isocomene)

3D-SDF for NP0064782 ((-)-Isocomene)

PDB for NP0064782 ((-)-Isocomene)

3D PDB for NP0064782 ((-)-Isocomene)

SMILES for NP0064782 ((-)-Isocomene)

INCHI for NP0064782 ((-)-Isocomene)

Structure for NP0064782 ((-)-Isocomene)

3D Structure for NP0064782 ((-)-Isocomene)