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Showing NP-Card for (+)-arnicenone (NP0167882)

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Record Information
Version1.0
Created at2022-09-03 03:33:58 UTC
Updated at2022-09-03 03:33:58 UTC
NP-MRD IDNP0167882
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-arnicenone
Description(+)-Arnicenone 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. (+)-arnicenone is found in Ligularia amplexicaulis. Based on a literature review very few articles have been published on (+)-Arnicenone.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0167882 ((+)-arnicenone)


  Mrv1652309032205332D          

 16 18  0  0  1  0            999 V2000
    1.7817   -0.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2968    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.7907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4506    0.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506    1.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6294    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843    1.2756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1392    2.0602    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6543    2.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9642    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192    1.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038    1.0206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5517    0.7907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2192    0.3057    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
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
M  END
Download

3D MOL for NP0167882 ((+)-arnicenone)

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3D SDF for NP0167882 ((+)-arnicenone)

  Mrv1652309032205332D          

 16 18  0  0  1  0            999 V2000
    1.7817   -0.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2968    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.7907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4506    0.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506    1.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6294    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843    1.2756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1392    2.0602    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6543    2.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9642    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192    1.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038    1.0206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5517    0.7907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2192    0.3057    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
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0167882

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-10-8-12(16)14(4)11(2)9-13(3)6-5-7-15(10,13)14/h9-10H,5-8H2,1-4H3/t10-,13+,14-,15-/m0/s1

> <INCHI_KEY>
RRCHUAUWSLVPRW-PUPMMZHASA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.34

> <EXACT_MASS>
218.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
25.611836059707702

> <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-en-4-one

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
3.446902848666667

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.897017193439833

> <JCHEM_PKA_STRONGEST_BASIC>
-7.568960024999736

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
66.3141

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,8R)-2,5,6,8-tetramethyltricyclo[6.3.0.0^{1,5}]undec-6-en-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0167882 ((+)-arnicenone)
Download
PDB for NP0167882 ((+)-arnicenone)
HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.326  -1.235   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.421   0.011   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.881   0.011   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.405   1.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.841   0.571   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.841   2.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.365   3.846   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.175   3.846   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.651   2.381   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.127   3.846   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.221   5.092   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.667   3.846   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.142   2.381   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.607   1.905   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.897   1.476   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.142   0.571   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6    9                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10   15                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    2    9   16                                             
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

Download
3D PDB for NP0167882 ((+)-arnicenone)
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SMILES for NP0167882 ((+)-arnicenone)
C[C@H]1CC(=O)[C@]2(C)C(C)=C[C@@]3(C)CCC[C@@]123
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INCHI for NP0167882 ((+)-arnicenone)
InChI=1S/C15H22O/c1-10-8-12(16)14(4)11(2)9-13(3)6-5-7-15(10,13)14/h9-10H,5-8H2,1-4H3/t10-,13+,14-,15-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H22O
Average Mass218.3400 Da
Monoisotopic Mass218.16707 Da
IUPAC Name(1S,2S,5R,8R)-2,5,6,8-tetramethyltricyclo[6.3.0.0^{1,5}]undec-6-en-4-one
Traditional Name(1S,2S,5R,8R)-2,5,6,8-tetramethyltricyclo[6.3.0.0^{1,5}]undec-6-en-4-one
CAS Registry NumberNot Available
SMILES
C[C@H]1CC(=O)[C@]2(C)C(C)=C[C@@]3(C)CCC[C@@]123
InChI Identifier
InChI=1S/C15H22O/c1-10-8-12(16)14(4)11(2)9-13(3)6-5-7-15(10,13)14/h9-10H,5-8H2,1-4H3/t10-,13+,14-,15-/m0/s1
InChI KeyRRCHUAUWSLVPRW-PUPMMZHASA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ligularia amplexicaulisLOTUS Database
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentAngular triquinanes  
Alternative Parents
Substituents
  • Angular triquinane sesquiterpenoid
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.12ALOGPS
logP3.45ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)19.9ChemAxon
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.31 m³·mol⁻¹ChemAxon
Polarizability25.61 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24846745  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound42608193  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]