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Showing NP-Card for 1alpha,5alpha-Epoxy-alpha-guaiene (NP0063526)

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Record Information
Version2.0
Created at2022-04-28 07:55:12 UTC
Updated at2022-04-28 07:55:12 UTC
NP-MRD IDNP0063526
Secondary Accession NumbersNone
Natural Product Identification
Common Name1alpha,5alpha-Epoxy-alpha-guaiene
Description(1S,2S,5R,7R,8S)-2,8-dimethyl-5-(prop-1-en-2-yl)-11-oxatricyclo[5.3.1.0¹,⁷]Undecane belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 1alpha,5alpha-Epoxy-alpha-guaiene is found in Cyperus rotundus . Based on a literature review very few articles have been published on (1S,2S,5R,7R,8S)-2,8-dimethyl-5-(prop-1-en-2-yl)-11-oxatricyclo[5.3.1.0¹,⁷]Undecane.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0063526 (1alpha,5alpha-Epoxy-alpha-guaiene)


  Mrv1652304282209552D          

 16 18  0  0  1  0            999 V2000
    1.1355    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  2  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0960    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7805   -0.5144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5848   -0.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5848    1.1558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7805    1.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992    1.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    2.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9150    1.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969   -1.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    0.4125    0.0000 O   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  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  6  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 10 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  7 15  1  6  0  0  0
  2 16  1  6  0  0  0
  1 16  1  1  0  0  0
M  END
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3D MOL for NP0063526 (1alpha,5alpha-Epoxy-alpha-guaiene)

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3D SDF for NP0063526 (1alpha,5alpha-Epoxy-alpha-guaiene)

  Mrv1652304282209552D          

 16 18  0  0  1  0            999 V2000
    1.1355    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  2  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0960    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7805   -0.5144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5848   -0.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5848    1.1558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7805    1.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992    1.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    2.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9150    1.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969   -1.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    0.4125    0.0000 O   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  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  6  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 10 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  7 15  1  6  0  0  0
  2 16  1  6  0  0  0
  1 16  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0063526

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@]23O[C@]12C[C@@H](CC[C@@H]3C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-10(2)13-6-5-11(3)14-8-7-12(4)15(14,9-13)16-14/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,14-,15+/m0/s1

> <INCHI_KEY>
RGRYQUWGSJPMMK-SBJFKYEJSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.356

> <EXACT_MASS>
220.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.453503284902926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,7R,8S)-2,8-dimethyl-5-(prop-1-en-2-yl)-11-oxatricyclo[5.3.1.0^{1,7}]undecane

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
3.910872351666667

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.25432013110417

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
66.068

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.50e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,7R,8S)-2,8-dimethyl-5-(prop-1-en-2-yl)-11-oxatricyclo[5.3.1.0^{1,7}]undecane

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0063526 (1alpha,5alpha-Epoxy-alpha-guaiene)
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PDB for NP0063526 (1alpha,5alpha-Epoxy-alpha-guaiene)
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       2.120   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.179   3.481   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.324  -0.960   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.825  -0.617   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.493   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.825   2.157   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.324   2.500   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.785   3.362   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.223   4.795   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.308   3.132   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.981  -2.462   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.453   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    5   11   16                                             
CONECT    2    1    3    7   16                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    2    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    1                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    7                                                            
CONECT   16    2    1                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

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3D PDB for NP0063526 (1alpha,5alpha-Epoxy-alpha-guaiene)
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SMILES for NP0063526 (1alpha,5alpha-Epoxy-alpha-guaiene)
C[C@H]1CC[C@@]23O[C@]12C[C@@H](CC[C@@H]3C)C(C)=C
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INCHI for NP0063526 (1alpha,5alpha-Epoxy-alpha-guaiene)
InChI=1S/C15H24O/c1-10(2)13-6-5-11(3)14-8-7-12(4)15(14,9-13)16-14/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,14-,15+/m0/s1
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SynonymsNot Available
Chemical FormulaC15H24O
Average Mass220.3560 Da
Monoisotopic Mass220.18272 Da
IUPAC Name(1S,2S,5R,7R,8S)-2,8-dimethyl-5-(prop-1-en-2-yl)-11-oxatricyclo[5.3.1.0^{1,7}]undecane
Traditional Name(1S,2S,5R,7R,8S)-2,8-dimethyl-5-(prop-1-en-2-yl)-11-oxatricyclo[5.3.1.0^{1,7}]undecane
CAS Registry NumberNot Available
SMILES
C[C@H]1CC[C@@]23O[C@]12C[C@@H](CC[C@@H]3C)C(C)=C
InChI Identifier
InChI=1S/C15H24O/c1-10(2)13-6-5-11(3)14-8-7-12(4)15(14,9-13)16-14/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,14-,15+/m0/s1
InChI KeyRGRYQUWGSJPMMK-SBJFKYEJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cyperus rotundusPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Sesquiterpenoid
    • 

  • Oxane
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP4.29ALOGPS
logP3.91ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.07 m³·mol⁻¹ChemAxon
Polarizability26.45 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound154496527  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available