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Showing NP-Card for (1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol (NP0217822)

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Record Information
Version2.0
Created at2022-09-05 18:17:00 UTC
Updated at2022-09-05 18:17:00 UTC
NP-MRD IDNP0217822
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol
DescriptionTrans-Sabinol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol is found in Achillea abrotanoides, Artemisia sericea, Brucea javanica, Daucus carota, Eupatorium capillifolium and Hedychium spicatum. (1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol was first documented in 2009 (PMID: 19768995). Based on a literature review a small amount of articles have been published on trans-Sabinol (PMID: 26404704) (PMID: 25765752) (PMID: 25103502).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0217822 ((1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)


  Mrv1652309052220172D          

 11 12  0  0  1  0            999 V2000
    1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3356    1.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    1.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1494    2.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
M  END
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3D MOL for NP0217822 ((1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)

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3D SDF for NP0217822 ((1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)

  Mrv1652309052220172D          

 11 12  0  0  1  0            999 V2000
    1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3356    1.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    1.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1494    2.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0217822

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@]12CC1C(=C)[C@H](O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8-9,11H,3-5H2,1-2H3/t8?,9-,10+/m1/s1

> <INCHI_KEY>
MDFQXBNVOAKNAY-XVBQNVSMSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.139157066793995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol

> <JCHEM_LOGP>
1.628784049666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.87382847462683

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5417874251982244

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
45.1653

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0217822 ((1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)
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PDB for NP0217822 ((1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)
HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.941  -1.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.626   2.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.158   3.108   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.279   4.193   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.910   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3    5                                                       
CONECT    5    4    3    6    9                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9    2   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0217822 ((1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)
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SMILES for NP0217822 ((1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)
CC(C)[C@@]12CC1C(=C)[C@H](O)C2
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INCHI for NP0217822 ((1s,3r)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8-9,11H,3-5H2,1-2H3/t8?,9-,10+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H16O
Average Mass152.2370 Da
Monoisotopic Mass152.12012 Da
IUPAC Name(1S,3R)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol
Traditional Name(1S,3R)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol
CAS Registry NumberNot Available
SMILES
CC(C)[C@@]12CC1C(=C)[C@H](O)C2
InChI Identifier
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8-9,11H,3-5H2,1-2H3/t8?,9-,10+/m1/s1
InChI KeyMDFQXBNVOAKNAY-XVBQNVSMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea abrotanoidesLOTUS Database
Artemisia sericeaLOTUS Database
Brucea javanicaLOTUS Database
Daucus carotaLOTUS Database
Eupatorium capillifoliumLOTUS Database
Hedychium spicatumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
    • 

  • Thujane monoterpenoid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • 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
logP1.63ChemAxon
pKa (Strongest Acidic)17.87ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.17 m³·mol⁻¹ChemAxon
Polarizability18.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000831  
Chemspider ID4934453  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6429076  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sampietro DA, Lizarraga EF, Ibatayev ZA, Omarova AB, Suleimen YM, Catalan CA: Chemical composition and antimicrobial activity of essential oils from Acantholippia deserticola, Artemisia proceriformis, Achillea micrantha and Libanotis buchtormensis against phytopathogenic bacteria and fungi. Nat Prod Res. 2016 Sep;30(17):1950-5. doi: 10.1080/14786419.2015.1091453. Epub  2015 Sep 24. [PubMed:26404704  ] 
  2. Radulovic NS, Mladenovic MZ, Randjelovic PJ, Stojanovic NM, Dekic MS, Blagojevic PD: Toxic essential oils. Part IV: The essential oil of Achillea falcata L. as a source of biologically/pharmacologically active trans-sabinyl esters. Food Chem Toxicol. 2015 Jun;80:114-129. doi: 10.1016/j.fct.2015.03.001. Epub 2015  Mar 9. [PubMed:25765752  ] 
  3. Venditti A, Maggi F, Vittori S, Papa F, Serrilli AM, Di Cecco M, Ciaschetti G, Mandrone M, Poli F, Bianco A: Volatile compounds from Achillea tenorii (Grande) growing in the Majella National Park (Italy). Nat Prod Res. 2014;28(20):1699-704. doi: 10.1080/14786419.2014.940349. Epub 2014  Aug 7. [PubMed:25103502  ] 
  4. Judzentiene A, Tomi F, Casanova J: Analysis of essential oils of Artemisia absinthium L. from Lithuania by CC, GC(RI), GC-MS and 13C NMR. Nat Prod Commun. 2009 Aug;4(8):1113-8. [PubMed:19768995  ] 
  5. LOTUS database [Link]