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Showing NP-Card for (2r,5s)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol (NP0328079)

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Record Information
Version2.0
Created at2022-09-12 11:13:29 UTC
Updated at2022-09-12 11:13:29 UTC
NP-MRD IDNP0328079
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,5s)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol
DescriptionBornane-2alpha,5beta-diol, also known as bornane-2α,5β-diol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (2r,5s)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol is found in Ferula sinaica. Based on a literature review very few articles have been published on Bornane-2alpha,5beta-diol.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0328079 ((2r,5s)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol)


  Mrv1652309122213132D          

 12 13  0  0  1  0            999 V2000
    0.2085    0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988    0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906   -0.2832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2239   -0.6957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.5418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6340    0.9543    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
M  END
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3D MOL for NP0328079 ((2r,5s)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol)

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3D SDF for NP0328079 ((2r,5s)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol)

  Mrv1652309122213132D          

 12 13  0  0  1  0            999 V2000
    0.2085    0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988    0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906   -0.2832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2239   -0.6957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.5418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6340    0.9543    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0328079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2C[C@@H](O)C1(C)C[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O2/c1-9(2)6-4-8(12)10(9,3)5-7(6)11/h6-8,11-12H,4-5H2,1-3H3/t6?,7-,8+,10?/m0/s1

> <INCHI_KEY>
HLVIHBJQDKVEAL-DOPNHTQNSA-N

> <FORMULA>
C10H18O2

> <MOLECULAR_WEIGHT>
170.252

> <EXACT_MASS>
170.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
19.348298061897736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,5S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol

> <JCHEM_LOGP>
0.6806930873333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.119470389230496

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.4750762988944

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8400291212195388

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
46.9068

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0328079 ((2r,5s)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol)
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PDB for NP0328079 ((2r,5s)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       0.389   0.683   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.864   0.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.389  -0.201   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.249   1.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.916   1.011   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.916  -0.529   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.418  -1.299   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.249  -1.299   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.249  -2.839   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.583  -0.529   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.583   1.011   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.917   1.781   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    8                                             
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0328079 ((2r,5s)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol)
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SMILES for NP0328079 ((2r,5s)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol)
CC1(C)C2C[C@@H](O)C1(C)C[C@@H]2O
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INCHI for NP0328079 ((2r,5s)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol)
InChI=1S/C10H18O2/c1-9(2)6-4-8(12)10(9,3)5-7(6)11/h6-8,11-12H,4-5H2,1-3H3/t6?,7-,8+,10?/m0/s1
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Synonyms
ValueSource
Bornane-2a,5b-diolGenerator
Bornane-2α,5β-diolGenerator
Chemical FormulaC10H18O2
Average Mass170.2520 Da
Monoisotopic Mass170.13068 Da
IUPAC Name(2R,5S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol
Traditional Name(2R,5S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol
CAS Registry NumberNot Available
SMILES
CC1(C)C2C[C@@H](O)C1(C)C[C@@H]2O
InChI Identifier
InChI=1S/C10H18O2/c1-9(2)6-4-8(12)10(9,3)5-7(6)11/h6-8,11-12H,4-5H2,1-3H3/t6?,7-,8+,10?/m0/s1
InChI KeyHLVIHBJQDKVEAL-DOPNHTQNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ferula sinaicaLOTUS 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
    • 

  • Bornane 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
logP0.68ChemAxon
pKa (Strongest Acidic)14.48ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.91 m³·mol⁻¹ChemAxon
Polarizability19.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID110554559  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91277640  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]