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Showing NP-Card for 3beta-3-Hydroxy-18-lupen-21-one (NP0048221)

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Record Information
Version2.0
Created at2022-03-17 20:53:02 UTC
Updated at2022-03-17 20:53:03 UTC
NP-MRD IDNP0048221
Secondary Accession NumbersNone
Natural Product Identification
Common Name3beta-3-Hydroxy-18-lupen-21-one
Description3Beta-3-Hydroxy-18-lupen-21-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3Beta-3-Hydroxy-18-lupen-21-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3beta-3-hydroxy-18-lupen-21-one has been detected, but not quantified in, several different foods, such as alcoholic beverages, beverages, coffee and coffee products, and tea. This could make 3beta-3-hydroxy-18-lupen-21-one a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048221 (3beta-3-Hydroxy-18-lupen-21-one)


  Mrv0541 02241208232D          

 32 36  0  0  0  0            999 V2000
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   -1.8992   -0.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 20 22  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
Download

3D MOL for NP0048221 (3beta-3-Hydroxy-18-lupen-21-one)

Download
3D SDF for NP0048221 (3beta-3-Hydroxy-18-lupen-21-one)

  Mrv0541 02241208232D          

 32 36  0  0  0  0            999 V2000
   -2.6147   -0.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6147   -1.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8992   -2.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849   -1.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849   -0.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8992   -0.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4692   -2.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2446   -1.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2446   -0.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4692   -0.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9575   -0.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9575    0.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2446    0.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4692    0.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    0.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6317    0.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9497    0.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7788    1.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9681    1.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518    2.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9681    2.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259    2.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315    1.9977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0407   -0.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9575   -1.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2446   -0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849   -0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3315   -2.1851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3127   -2.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4869   -2.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745   -0.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411   -0.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
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  9 11  1  0  0  0  0
  9 26  1  0  0  0  0
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 12 13  1  0  0  0  0
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 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
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 16 19  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2C3CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O2/c1-18(2)24-20(31)17-27(5)15-16-29(7)19(25(24)27)9-10-22-28(6)13-12-23(32)26(3,4)21(28)11-14-30(22,29)8/h18-19,21-23,32H,9-17H2,1-8H3

> <INCHI_KEY>
FLGCQFQUEPUAMZ-UHFFFAOYSA-N

> <FORMULA>
C30H48O2

> <MOLECULAR_WEIGHT>
440.7009

> <EXACT_MASS>
440.36543078

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
54.27177307551817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
17-hydroxy-1,2,5,14,18,18-hexamethyl-8-(propan-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-8-en-7-one

> <ALOGPS_LOGP>
6.32

> <JCHEM_LOGP>
6.679171624666667

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.489433390176508

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351018921823846

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
132.40739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-hydroxy-8-isopropyl-1,2,5,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-8-en-7-one

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0048221 (3beta-3-Hydroxy-18-lupen-21-one)
Download
PDB for NP0048221 (3beta-3-Hydroxy-18-lupen-21-one)
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      -4.881  -1.763   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.881  -3.307   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.545  -4.079   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.212  -3.307   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.212  -1.763   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.545  -0.993   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.876  -4.079   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.457  -3.307   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.457  -1.763   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.876  -0.993   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.787  -0.993   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.787   0.543   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.457   1.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.876   0.543   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.183   0.327   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.046   1.348   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.506   1.088   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.187   2.578   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.674   2.741   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.897   4.079   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.674   5.415   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.355   4.076   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.219   3.729   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.676  -0.072   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.787  -2.537   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.457  -0.224   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.212  -0.224   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.219  -4.079   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -4.317  -5.415   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.776  -5.415   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.126  -1.765   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.183  -1.083   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   28                                                  
CONECT    3    2    4   29   30                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   27                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   26                                             
CONECT   10    5    9   14                                                  
CONECT   11    9   12   25   31                                             
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   16   17   24   32                                             
CONECT   16   12   15   19                                                  
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   16   18   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18                                                            
CONECT   24   15                                                            
CONECT   25   11                                                            
CONECT   26    9                                                            
CONECT   27    5                                                            
CONECT   28    2                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31   11   32                                                       
CONECT   32   15   31                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

Download
3D PDB for NP0048221 (3beta-3-Hydroxy-18-lupen-21-one)
Download
SMILES for NP0048221 (3beta-3-Hydroxy-18-lupen-21-one)
CC(C)C1=C2C3CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)CC1=O
Download
INCHI for NP0048221 (3beta-3-Hydroxy-18-lupen-21-one)
InChI=1S/C30H48O2/c1-18(2)24-20(31)17-27(5)15-16-29(7)19(25(24)27)9-10-22-28(6)13-12-23(32)26(3,4)21(28)11-14-30(22,29)8/h18-19,21-23,32H,9-17H2,1-8H3
Download
View in JSmol
Synonyms
ValueSource
3b-3-Hydroxy-18-lupen-21-oneGenerator
3Β-3-hydroxy-18-lupen-21-oneGenerator
Chemical FormulaC30H48O2
Average Mass440.7009 Da
Monoisotopic Mass440.36543 Da
IUPAC Name17-hydroxy-1,2,5,14,18,18-hexamethyl-8-(propan-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-8-en-7-one
Traditional Name17-hydroxy-8-isopropyl-1,2,5,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicos-8-en-7-one
CAS Registry Number29367-66-6
SMILES
CC(C)C1=C2C3CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)CC1=O
InChI Identifier
InChI=1S/C30H48O2/c1-18(2)24-20(31)17-27(5)15-16-29(7)19(25(24)27)9-10-22-28(6)13-12-23(32)26(3,4)21(28)11-14-30(22,29)8/h18-19,21-23,32H,9-17H2,1-8H3
InChI KeyFLGCQFQUEPUAMZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • 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 triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative ParentsNot Available
SubstituentsNot Available
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
logP6.32ALOGPS
logP6.68ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity132.41 m³·mol⁻¹ChemAxon
Polarizability54.27 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035355  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014027  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound77220501  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References