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Showing NP-Card for Anastreptene (NP0064293)

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Record Information
Version2.0
Created at2022-04-28 08:33:14 UTC
Updated at2022-04-28 08:33:14 UTC
NP-MRD IDNP0064293
Secondary Accession NumbersNone
Natural Product Identification
Common NameAnastreptene
Description(1S,2R,4S,7S,8R)-3,3,7,11-tetramethyltetracyclo[5.4.0.0¹,⁸.0²,⁴]Undec-10-ene belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Anastreptene is found in Anastrepta orcadensis, Calypogeia suecica, Diplophyllum albicans, Marsupella alpina, Marsupella emarginata, Scapania aequiloba, Scapania aspera, Scapania nemorosa, Scapania paludosa, Scapania undulata, Tritomaria quinquedentata and Tritomaria quinquedentata (Huds.). Based on a literature review very few articles have been published on (1S,2R,4S,7S,8R)-3,3,7,11-tetramethyltetracyclo[5.4.0.0¹,⁸.0²,⁴]Undec-10-ene.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0064293 (Anastreptene)


  Mrv1652304282210332D          

 15 18  0  0  1  0            999 V2000
    0.3331   -0.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1457   -0.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609    0.0437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5196    0.4058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0538   -0.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039    0.8667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8881    1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294    0.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6865    0.1425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0022   -0.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7435   -0.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7287   -1.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5136   -0.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7388   -1.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
 10  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  6 14  1  1  0  0  0
  2 15  1  0  0  0  0
M  END
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3D MOL for NP0064293 (Anastreptene)

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3D SDF for NP0064293 (Anastreptene)

  Mrv1652304282210332D          

 15 18  0  0  1  0            999 V2000
    0.3331   -0.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1457   -0.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609    0.0437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5196    0.4058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0538   -0.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039    0.8667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8881    1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294    0.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6865    0.1425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0022   -0.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7435   -0.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7287   -1.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5136   -0.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7388   -1.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
 10  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  6 14  1  1  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0064293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@@H]2[C@]3(C)CC[C@H]4[C@H](C4(C)C)[C@]123

> <INCHI_IDENTIFIER>
InChI=1S/C15H22/c1-9-5-6-11-14(4)8-7-10-12(13(10,2)3)15(9,11)14/h5,10-12H,6-8H2,1-4H3/t10-,11+,12+,14-,15-/m0/s1

> <INCHI_KEY>
SYNYVXGDEQOMCB-HPYVJYLESA-N

> <FORMULA>
C15H22

> <MOLECULAR_WEIGHT>
202.341

> <EXACT_MASS>
202.172150708

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
60.6561388940169

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4S,7S,8R)-3,3,7,11-tetramethyltetracyclo[5.4.0.0^{1,8}.0^{2,4}]undec-10-ene

> <ALOGPS_LOGP>
3.83

> <JCHEM_LOGP>
3.3353611699999997

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
63.71389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,7S,8R)-3,3,7,11-tetramethyltetracyclo[5.4.0.0^{1,8}.0^{2,4}]undec-10-ene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0064293 (Anastreptene)
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PDB for NP0064293 (Anastreptene)
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       0.622  -1.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.139  -1.443   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.354   0.082   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.970   0.757   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.100  -0.350   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.247   1.618   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.524   2.478   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.908   1.802   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.015   0.266   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.738  -0.594   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.121  -1.270   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.094  -2.810   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.559  -1.823   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.387   2.895   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.246  -2.514   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2    4    6   10                                             
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    3    7   14                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    3   11                                                  
CONECT   11   10    9   12   13                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6                                                            
CONECT   15    2                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   36    0
END

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3D PDB for NP0064293 (Anastreptene)
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SMILES for NP0064293 (Anastreptene)
CC1=CC[C@@H]2[C@]3(C)CC[C@H]4[C@H](C4(C)C)[C@]123
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INCHI for NP0064293 (Anastreptene)
InChI=1S/C15H22/c1-9-5-6-11-14(4)8-7-10-12(13(10,2)3)15(9,11)14/h5,10-12H,6-8H2,1-4H3/t10-,11+,12+,14-,15-/m0/s1
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SynonymsNot Available
Chemical FormulaC15H22
Average Mass202.3410 Da
Monoisotopic Mass202.17215 Da
IUPAC Name(1S,2R,4S,7S,8R)-3,3,7,11-tetramethyltetracyclo[5.4.0.0^{1,8}.0^{2,4}]undec-10-ene
Traditional Name(1S,2R,4S,7S,8R)-3,3,7,11-tetramethyltetracyclo[5.4.0.0^{1,8}.0^{2,4}]undec-10-ene
CAS Registry NumberNot Available
SMILES
CC1=CC[C@@H]2[C@]3(C)CC[C@H]4[C@H](C4(C)C)[C@]123
InChI Identifier
InChI=1S/C15H22/c1-9-5-6-11-14(4)8-7-10-12(13(10,2)3)15(9,11)14/h5,10-12H,6-8H2,1-4H3/t10-,11+,12+,14-,15-/m0/s1
InChI KeySYNYVXGDEQOMCB-HPYVJYLESA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anastrepta orcadensisPlant
Calypogeia suecicaPlant
Diplophyllum albicansPlant
Marsupella alpinaPlant
Marsupella emarginataPlant
Scapania aequilobaPlant
Scapania asperaPlant
Scapania nemoreaPlant
Scapania paludosaPlant
Scapania undulataPlant
Trilophozia quinquedentataLOTUS Database
Tritomaria quinquedentata (Huds.)Plant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct Parent5,10-cycloaromadendrane sesquiterpenoids  
Alternative Parents
Substituents
  • 5,10-cycloaromadendrane sesquiterpenoid
    • 

  • Branched unsaturated hydrocarbon
    • 

  • Polycyclic hydrocarbon
    • 

  • Cyclic olefin
    • 

  • Unsaturated aliphatic hydrocarbon
    • 

  • Unsaturated hydrocarbon
    • 

  • Olefin
    • 

  • Hydrocarbon
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP3.83ALOGPS
logP3.34ChemAxon
logS-4.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity63.71 m³·mol⁻¹ChemAxon
Polarizability60.66 ųChemAxon
Number of Rings4ChemAxon
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 Compound163106075  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available