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Showing NP-Card for Epioxylubimin (NP0048272)

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Record Information
Version2.0
Created at2022-03-17 20:53:50 UTC
Updated at2022-03-17 20:53:50 UTC
NP-MRD IDNP0048272
Secondary Accession NumbersNone
Natural Product Identification
Common NameEpioxylubimin
DescriptionEpioxylubimin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Epioxylubimin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Epioxylubimin has been detected, but not quantified in, potato. Epioxylubimin is found in Datura stramonium. This could make epioxylubimin a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048272 (Epioxylubimin)


  Mrv0541 02241211252D          

 18 19  0  0  0  0            999 V2000
    0.7281    2.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2139    1.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228    1.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9706    0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    0.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422   -0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9706   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5370    0.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990    0.8490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900    0.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751   -0.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751   -1.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0228   -1.8206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281   -1.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0809   -1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660   -1.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660   -2.3871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  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
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
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3D MOL for NP0048272 (Epioxylubimin)

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3D SDF for NP0048272 (Epioxylubimin)

  Mrv0541 02241211252D          

 18 19  0  0  0  0            999 V2000
    0.7281    2.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2139    1.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228    1.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9706    0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    0.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422   -0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9706   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5370    0.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990    0.8490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900    0.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751   -0.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751   -1.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0228   -1.8206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281   -1.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0809   -1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660   -1.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660   -2.3871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  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
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048272

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(O)C(O)CC(C=O)C11CCC(C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O3/c1-9(2)11-4-5-15(7-11)10(3)14(18)13(17)6-12(15)8-16/h8,10-14,17-18H,1,4-7H2,2-3H3

> <INCHI_KEY>
YIGYYGXJIDAEOF-UHFFFAOYSA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.3493

> <EXACT_MASS>
252.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.30990410856134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8,9-dihydroxy-10-methyl-2-(prop-1-en-2-yl)spiro[4.5]decane-6-carbaldehyde

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
1.3183296336666668

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.020908557546367

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.69063994752619

> <JCHEM_PKA_STRONGEST_BASIC>
-3.159691098782803

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
70.3223

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,9-dihydroxy-10-methyl-2-(prop-1-en-2-yl)spiro[4.5]decane-6-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0048272 (Epioxylubimin)
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PDB for NP0048272 (Epioxylubimin)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.359   4.456   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.266   3.247   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.776   3.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.812   1.736   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.452   1.132   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.452  -0.377   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.812  -0.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.869   0.527   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.171   1.585   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.661   1.282   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.207  -0.226   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.567  -0.981   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.567  -2.492   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.776  -3.399   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.359  -2.794   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.151  -1.888   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.057  -2.946   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.057  -4.456   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11   16                                             
CONECT    7    6    8                                                       
CONECT    8    4    7                                                       
CONECT    9   10                                                            
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16    6   15   17                                                  
CONECT   17   13   16   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

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3D PDB for NP0048272 (Epioxylubimin)
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SMILES for NP0048272 (Epioxylubimin)
CC1C(O)C(O)CC(C=O)C11CCC(C1)C(C)=C
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INCHI for NP0048272 (Epioxylubimin)
InChI=1S/C15H24O3/c1-9(2)11-4-5-15(7-11)10(3)14(18)13(17)6-12(15)8-16/h8,10-14,17-18H,1,4-7H2,2-3H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H24O3
Average Mass252.3493 Da
Monoisotopic Mass252.17254 Da
IUPAC Name8,9-dihydroxy-10-methyl-2-(prop-1-en-2-yl)spiro[4.5]decane-6-carbaldehyde
Traditional Name8,9-dihydroxy-10-methyl-2-(prop-1-en-2-yl)spiro[4.5]decane-6-carbaldehyde
CAS Registry Number69350-60-3
SMILES
CC1C(O)C(O)CC(C=O)C11CCC(C1)C(C)=C
InChI Identifier
InChI=1S/C15H24O3/c1-9(2)11-4-5-15(7-11)10(3)14(18)13(17)6-12(15)8-16/h8,10-14,17-18H,1,4-7H2,2-3H3
InChI KeyYIGYYGXJIDAEOF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Datura stramoniumLOTUS Database
Solanum tuberosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
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
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • 1,2-diol
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aldehyde
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
logP1.33ALOGPS
logP1.32ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)13.69ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.32 m³·mol⁻¹ChemAxon
Polarizability28.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035613  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014316  
KNApSAcK IDNot Available
Chemspider ID24785695  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14565572  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References