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Showing NP-Card for 8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol (NP0224472)

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Record Information
Version2.0
Created at2022-09-06 02:50:04 UTC
Updated at2022-09-06 02:50:04 UTC
NP-MRD IDNP0224472
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol
Description1,5-Dimethyl-11-methylidene-8-(propan-2-yl)-15-oxabicyclo[10.2.1]Pentadeca-2,6-dien-5-ol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol is found in Nicotiana sylvestris and Nicotiana tabacum. 1,5-Dimethyl-11-methylidene-8-(propan-2-yl)-15-oxabicyclo[10.2.1]Pentadeca-2,6-dien-5-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0224472 (8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol)


  Mrv1533004231520052D          

 22 23  0  0  0  0            999 V2000
    4.8803   -0.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1677   -0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1713   -1.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514   -0.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7387   -0.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9362   -0.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1300   -0.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978   -1.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143    0.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5382    0.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8347    0.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2989    1.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4945    1.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    0.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    2.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7278    1.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4405    2.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1567    1.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4355    2.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9698    1.5645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604    0.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4477    0.4635    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
 15 12  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 18  1  4  0  0  0
 21 22  2  0  0  0  0
  4 22  1  0  0  0  0
M  END
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3D MOL for NP0224472 (8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol)

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3D SDF for NP0224472 (8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol)

  Mrv1533004231520052D          

 22 23  0  0  0  0            999 V2000
    4.8803   -0.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1677   -0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1713   -1.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514   -0.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7387   -0.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9362   -0.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1300   -0.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978   -1.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143    0.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5382    0.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8347    0.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2989    1.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4945    1.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    0.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    2.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7278    1.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4405    2.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1567    1.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4355    2.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9698    1.5645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604    0.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4477    0.4635    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
 15 12  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 18  1  4  0  0  0
 21 22  2  0  0  0  0
  4 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224472

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CCC(=C)C2CCC(C)(O2)C=CCC(C)(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O2/c1-15(2)17-8-7-16(3)18-10-14-20(5,22-18)12-6-11-19(4,21)13-9-17/h6,9,12-13,15,17-18,21H,3,7-8,10-11,14H2,1-2,4-5H3

> <INCHI_KEY>
SOCRUWBAQPJTHY-UHFFFAOYSA-N

> <FORMULA>
C20H32O2

> <MOLECULAR_WEIGHT>
304.474

> <EXACT_MASS>
304.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
36.36132828355986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5-dimethyl-11-methylidene-8-(propan-2-yl)-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
4.488521847666666

> <ALOGPS_LOGS>
-5.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.410688235585894

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3064618666701855

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
94.9843

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0224472 (8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol)
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PDB for NP0224472 (8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol)
HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       9.110  -0.663   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.780  -1.439   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.786  -2.979   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.443  -0.675   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.112  -1.451   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.614  -0.679   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.109  -1.006   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.489  -2.415   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.333   0.325   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.871   0.242   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.425   1.679   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.425   3.158   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.923   3.500   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.359   1.474   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.755   3.933   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.092   3.169   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.422   3.945   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.759   3.181   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.280   4.630   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.277   2.920   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.766   1.641   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.436   0.865   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12    9                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21    4                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

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3D PDB for NP0224472 (8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol)
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SMILES for NP0224472 (8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol)
CC(C)C1CCC(=C)C2CCC(C)(O2)C=CCC(C)(O)C=C1
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INCHI for NP0224472 (8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol)
InChI=1S/C20H32O2/c1-15(2)17-8-7-16(3)18-10-14-20(5,22-18)12-6-11-19(4,21)13-9-17/h6,9,12-13,15,17-18,21H,3,7-8,10-11,14H2,1-2,4-5H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H32O2
Average Mass304.4740 Da
Monoisotopic Mass304.24023 Da
IUPAC Name1,5-dimethyl-11-methylidene-8-(propan-2-yl)-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol
Traditional Name8-isopropyl-1,5-dimethyl-11-methylidene-15-oxabicyclo[10.2.1]pentadeca-2,6-dien-5-ol
CAS Registry NumberNot Available
SMILES
CC(C)C1CCC(=C)C2CCC(C)(O2)C=CCC(C)(O)C=C1
InChI Identifier
InChI=1S/C20H32O2/c1-15(2)17-8-7-16(3)18-10-14-20(5,22-18)12-6-11-19(4,21)13-9-17/h6,9,12-13,15,17-18,21H,3,7-8,10-11,14H2,1-2,4-5H3
InChI KeySOCRUWBAQPJTHY-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Nicotiana sylvestrisLOTUS Database
Nicotiana tabacumLOTUS Database
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
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • 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
logP4.54ALOGPS
logP4.49ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)18.41ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.98 m³·mol⁻¹ChemAxon
Polarizability36.36 ųChemAxon
Number of Rings2ChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]