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Showing NP-Card for (1R-endo)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one (NP0057818)

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Record Information
Version2.0
Created at2022-04-28 03:11:57 UTC
Updated at2022-04-28 03:11:57 UTC
NP-MRD IDNP0057818
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1R-endo)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one
Description(1R,3R,4R)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethylbicyclo[2.2.1]Heptan-2-one belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (1R-endo)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one is found in Florestina tripteris. Based on a literature review very few articles have been published on (1R,3R,4R)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethylbicyclo[2.2.1]Heptan-2-one.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0057818 ((1R-endo)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one)


  Mrv1652304282205112D          

 13 14  0  0  1  0            999 V2000
    1.0875    0.9834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3514    0.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1555    1.3840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2955   -0.3065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1329   -0.6660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8357   -0.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131    0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3164    0.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498   -0.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888    0.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -1.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428   -2.1148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1379   -1.1424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  2  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
  1  7  1  0  0  0  0
  5  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  6  0  0  0
 11 12  1  0  0  0  0
  4 13  1  1  0  0  0
M  END
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3D MOL for NP0057818 ((1R-endo)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one)

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3D SDF for NP0057818 ((1R-endo)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one)

  Mrv1652304282205112D          

 13 14  0  0  1  0            999 V2000
    1.0875    0.9834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3514    0.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1555    1.3840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2955   -0.3065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1329   -0.6660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8357   -0.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131    0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3164    0.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498   -0.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888    0.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -1.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428   -2.1148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1379   -1.1424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  2  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
  1  7  1  0  0  0  0
  5  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  6  0  0  0
 11 12  1  0  0  0  0
  4 13  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0057818

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2CC[C@@]1(CO)[C@@H](O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O3/c1-9(2)6-3-4-10(9,5-11)8(13)7(6)12/h6,8,11,13H,3-5H2,1-2H3/t6-,8-,10+/m0/s1

> <INCHI_KEY>
FGYKCTBCCDITGJ-KADJCCMJSA-N

> <FORMULA>
C10H16O3

> <MOLECULAR_WEIGHT>
184.235

> <EXACT_MASS>
184.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.201377763393886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,4R)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one

> <ALOGPS_LOGP>
0.27

> <JCHEM_LOGP>
0.30108879066666644

> <ALOGPS_LOGS>
-0.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.095785454366716

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.868403634786706

> <JCHEM_PKA_STRONGEST_BASIC>
-2.799897553204908

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
47.57899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.47e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4R)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0057818 ((1R-endo)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one)
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PDB for NP0057818 ((1R-endo)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one)
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       2.030   1.836   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.656   1.238   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.290   2.584   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.552  -0.572   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.115  -1.243   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.427  -0.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.384   1.103   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.457   0.307   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.213  -1.091   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.912   0.403   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.419  -2.887   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.627  -3.948   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.257  -2.133   0.000  0.00  0.00           O+0
CONECT    1    2    7    8                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6    8   11                                             
CONECT    6    5    7                                                       
CONECT    7    6    1                                                       
CONECT    8    5    1    9   10                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12                                                       
CONECT   12   11                                                            
CONECT   13    4                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0057818 ((1R-endo)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one)
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SMILES for NP0057818 ((1R-endo)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one)
CC1(C)[C@H]2CC[C@@]1(CO)[C@@H](O)C2=O
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INCHI for NP0057818 ((1R-endo)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one)
InChI=1S/C10H16O3/c1-9(2)6-3-4-10(9,5-11)8(13)7(6)12/h6,8,11,13H,3-5H2,1-2H3/t6-,8-,10+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H16O3
Average Mass184.2350 Da
Monoisotopic Mass184.10994 Da
IUPAC Name(1R,3R,4R)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one
Traditional Name(1R,3R,4R)-3-hydroxy-4-(hydroxymethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one
CAS Registry NumberNot Available
SMILES
CC1(C)[C@H]2CC[C@@]1(CO)[C@@H](O)C2=O
InChI Identifier
InChI=1S/C10H16O3/c1-9(2)6-3-4-10(9,5-11)8(13)7(6)12/h6,8,11,13H,3-5H2,1-2H3/t6-,8-,10+/m0/s1
InChI KeyFGYKCTBCCDITGJ-KADJCCMJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Florestina tripterisPlant
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
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP0.27ALOGPS
logP0.3ChemAxon
logS-0.39ALOGPS
pKa (Strongest Acidic)12.87ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.58 m³·mol⁻¹ChemAxon
Polarizability20.2 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162923489  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available