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Showing NP-Card for Oleanolic aldehyde (NP0047994)

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Record Information
Version2.0
Created at2022-03-17 20:49:20 UTC
Updated at2022-03-17 20:49:21 UTC
NP-MRD IDNP0047994
Secondary Accession NumbersNone
Natural Product Identification
Common NameOleanolic aldehyde
DescriptionOleanolic aldehyde belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Oleanolic aldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Oleanolic aldehyde has been detected, but not quantified in, common grapes and fruits. Oleanolic aldehyde is found in Agastache rugosa, Buddleja asiatica, Hippophae rhamnoides, Lawsonia inermis, Mammillaria longimamma, Melaleuca ericifolia, Ocimum basilicum , Paeonia lactiflora, Phoradendron brachystachyum, Pistacia terebinthus, Quercus suber and Vitis vinifera. This could make oleanolic aldehyde a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047994 (Oleanolic aldehyde)


  Mrv0541 05061307512D          

 32 36  0  0  0  0            999 V2000
    7.1280    3.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0674    3.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7806   -1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8411   -1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254    1.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1688   -0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899   -0.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4543    1.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398    1.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398   -1.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109    0.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4543   -0.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3122    2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3122    1.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5977    0.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833    2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3122    1.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1688    1.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833    1.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254   -0.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7399    0.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -0.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5977    3.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109   -1.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1688    0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4543    0.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5978    1.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0267    1.4575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820   -1.0175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 20  8  2  0  0  0  0
 21 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 10  1  0  0  0  0
 23  9  1  0  0  0  0
 24 11  1  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 25 14  1  0  0  0  0
 25 18  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 22  1  0  0  0  0
 26 24  1  0  0  0  0
 27  5  1  0  0  0  0
 27 12  1  0  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28  6  1  0  0  0  0
 28 15  1  0  0  0  0
 28 20  1  0  0  0  0
 29  7  1  0  0  0  0
 29 13  1  0  0  0  0
 29 23  1  0  0  0  0
 29 28  1  0  0  0  0
 30 16  1  0  0  0  0
 30 17  1  0  0  0  0
 30 19  1  0  0  0  0
 30 21  1  0  0  0  0
 31 19  2  0  0  0  0
 32 24  1  0  0  0  0
M  END
Download

3D MOL for NP0047994 (Oleanolic aldehyde)

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3D SDF for NP0047994 (Oleanolic aldehyde)

  Mrv0541 05061307512D          

 32 36  0  0  0  0            999 V2000
    7.1280    3.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0674    3.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7806   -1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8411   -1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254    1.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1688   -0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899   -0.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4543    1.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398    1.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398   -1.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109    0.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4543   -0.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3122    2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3122    1.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5977    0.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833    2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3122    1.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1688    1.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833    1.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254   -0.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7399    0.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -0.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5977    3.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109   -1.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1688    0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4543    0.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5978    1.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0267    1.4575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820   -1.0175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 20  8  2  0  0  0  0
 21 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 10  1  0  0  0  0
 23  9  1  0  0  0  0
 24 11  1  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 25 14  1  0  0  0  0
 25 18  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 22  1  0  0  0  0
 26 24  1  0  0  0  0
 27  5  1  0  0  0  0
 27 12  1  0  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28  6  1  0  0  0  0
 28 15  1  0  0  0  0
 28 20  1  0  0  0  0
 29  7  1  0  0  0  0
 29 13  1  0  0  0  0
 29 23  1  0  0  0  0
 29 28  1  0  0  0  0
 30 16  1  0  0  0  0
 30 17  1  0  0  0  0
 30 19  1  0  0  0  0
 30 21  1  0  0  0  0
 31 19  2  0  0  0  0
 32 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047994

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O2/c1-25(2)14-16-30(19-31)17-15-28(6)20(21(30)18-25)8-9-23-27(5)12-11-24(32)26(3,4)22(27)10-13-29(23,28)7/h8,19,21-24,32H,9-18H2,1-7H3

> <INCHI_KEY>
STHRNDDZYFUIDO-UHFFFAOYSA-N

> <FORMULA>
C30H48O2

> <MOLECULAR_WEIGHT>
440.7009

> <EXACT_MASS>
440.36543078

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
53.98941139762954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carbaldehyde

> <ALOGPS_LOGP>
6.57

> <JCHEM_LOGP>
6.436217181000001

> <ALOGPS_LOGS>
-6.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.489433291560097

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351216477714746

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
132.69909999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.33e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047994 (Oleanolic aldehyde)
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PDB for NP0047994 (Oleanolic aldehyde)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      13.306   6.980   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.326   6.980   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.324  -3.079   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.303  -3.079   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.647   1.951   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.648  -0.359   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.941  -0.996   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.315   3.491   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.981   2.721   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.981  -1.899   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.980   0.411   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.314   1.181   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.315  -1.129   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.649   5.031   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.982   0.411   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.649   3.490   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.316   1.181   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.982   5.031   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.649   1.951   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.648   2.721   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.982   3.491   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.647  -1.130   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.981   1.181   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.980  -1.129   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.316   5.801   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.314  -1.900   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.647   0.411   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.648   1.180   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.315   0.410   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.316   2.720   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.983   2.721   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.646  -1.899   0.000  0.00  0.00           O+0
CONECT    1   25                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8    9   20                                                       
CONECT    9    8   23                                                       
CONECT   10   13   22                                                       
CONECT   11   12   24                                                       
CONECT   12   11   27                                                       
CONECT   13   10   29                                                       
CONECT   14   16   25                                                       
CONECT   15   17   28                                                       
CONECT   16   14   30                                                       
CONECT   17   15   30                                                       
CONECT   18   21   25                                                       
CONECT   19   30   31                                                       
CONECT   20    8   21   28                                                  
CONECT   21   18   20   30                                                  
CONECT   22   10   26   27                                                  
CONECT   23    9   27   29                                                  
CONECT   24   11   26   32                                                  
CONECT   25    1    2   14   18                                             
CONECT   26    3    4   22   24                                             
CONECT   27    5   12   22   23                                             
CONECT   28    6   15   20   29                                             
CONECT   29    7   13   23   28                                             
CONECT   30   16   17   19   21                                             
CONECT   31   19                                                            
CONECT   32   24                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

Download
3D PDB for NP0047994 (Oleanolic aldehyde)
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SMILES for NP0047994 (Oleanolic aldehyde)
CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1)C=O
Download
INCHI for NP0047994 (Oleanolic aldehyde)
InChI=1S/C30H48O2/c1-25(2)14-16-30(19-31)17-15-28(6)20(21(30)18-25)8-9-23-27(5)12-11-24(32)26(3,4)22(27)10-13-29(23,28)7/h8,19,21-24,32H,9-18H2,1-7H3
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View in JSmol
Synonyms
ValueSource
3b-Hydroxy-12-oleanen-28-alHMDB
Chemical FormulaC30H48O2
Average Mass440.7009 Da
Monoisotopic Mass440.36543 Da
IUPAC Name10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carbaldehyde
Traditional Name10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carbaldehyde
CAS Registry Number17020-22-3
SMILES
CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1)C=O
InChI Identifier
InChI=1S/C30H48O2/c1-25(2)14-16-30(19-31)17-15-28(6)20(21(30)18-25)8-9-23-27(5)12-11-24(32)26(3,4)22(27)10-13-29(23,28)7/h8,19,21-24,32H,9-18H2,1-7H3
InChI KeySTHRNDDZYFUIDO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agastache rugosaLOTUS Database
Buddleja asiaticaLOTUS Database
Hippophae rhamnoidesLOTUS Database
Lawsonia inermisLOTUS Database
Mammillaria longimammaLOTUS Database
Melaleuca ericifoliaLOTUS Database
Ocimum basilicumPlant
Paeonia lactifloraLOTUS Database
Phoradendron brachystachyumLOTUS Database
Pistacia terebinthusLOTUS Database
Quercus suberLOTUS Database
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
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 Parents
Substituents
  • Triterpenoid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aldehyde
    • 

  • 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
logP6.57ALOGPS
logP6.44ChemAxon
logS-6.5ALOGPS
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
Refractivity132.7 m³·mol⁻¹ChemAxon
Polarizability53.99 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034511  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013010  
KNApSAcK IDNot Available
Chemspider ID11517234  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14423516  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References