NP-MRD: Showing NP-Card for 20beta-Hydroxyursolic acid (NP0048154)

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Record Information

Version

2.0

Created at

2022-03-17 20:51:57 UTC

Updated at

2022-03-17 20:51:58 UTC

NP-MRD ID

NP0048154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20beta-Hydroxyursolic acid

Description

20Beta-Hydroxyursolic acid, also known as 20b-hydroxyursolate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 20Beta-Hydroxyursolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 20beta-Hydroxyursolic acid has been detected, but not quantified in, black elderberries and pomes. This could make 20beta-hydroxyursolic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308142D          

 34 38  0  0  0  0            999 V2000
    3.5358    2.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2082   -2.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1476   -2.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924    0.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358   -0.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7855    0.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4345    3.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213    1.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    0.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068   -1.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366   -0.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779   -0.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -1.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2502   -0.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792    1.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647   -0.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792    1.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2503    1.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358    0.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -1.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1069   -0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366   -1.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2503    1.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792    0.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779   -1.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -0.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358   -0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647    2.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9648    0.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7510   -1.7487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3937    0.7264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -0.5111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4951    3.0083    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
 18  1  1  0  0  0  0
 19  8  2  0  0  0  0
 20 10  1  0  0  0  0
 21  9  1  0  0  0  0
 22 11  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  1  0  0  0  0
 25  2  1  0  0  0  0
 25  3  1  0  0  0  0
 25 20  1  0  0  0  0
 25 22  1  0  0  0  0
 26  4  1  0  0  0  0
 26 12  1  0  0  0  0
 26 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27  5  1  0  0  0  0
 27 14  1  0  0  0  0
 27 19  1  0  0  0  0
 28  6  1  0  0  0  0
 28 13  1  0  0  0  0
 28 21  1  0  0  0  0
 28 27  1  0  0  0  0
 29  7  1  0  0  0  0
 29 15  1  0  0  0  0
 29 18  1  0  0  0  0
 30 16  1  0  0  0  0
 30 17  1  0  0  0  0
 30 23  1  0  0  0  0
 30 24  1  0  0  0  0
 31 22  1  0  0  0  0
 32 24  2  0  0  0  0
 33 24  1  0  0  0  0
 34 29  1  0  0  0  0
M  END


  Mrv0541 05061308142D          

 34 38  0  0  0  0            999 V2000
    3.5358    2.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2082   -2.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1476   -2.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924    0.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358   -0.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7855    0.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4345    3.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213    1.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    0.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068   -1.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366   -0.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779   -0.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -1.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2502   -0.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792    1.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647   -0.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792    1.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2503    1.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358    0.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -1.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1069   -0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366   -1.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2503    1.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792    0.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779   -1.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -0.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358   -0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647    2.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9648    0.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7510   -1.7487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3937    0.7264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -0.5111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4951    3.0083    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
 18  1  1  0  0  0  0
 19  8  2  0  0  0  0
 20 10  1  0  0  0  0
 21  9  1  0  0  0  0
 22 11  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  1  0  0  0  0
 25  2  1  0  0  0  0
 25  3  1  0  0  0  0
 25 20  1  0  0  0  0
 25 22  1  0  0  0  0
 26  4  1  0  0  0  0
 26 12  1  0  0  0  0
 26 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27  5  1  0  0  0  0
 27 14  1  0  0  0  0
 27 19  1  0  0  0  0
 28  6  1  0  0  0  0
 28 13  1  0  0  0  0
 28 21  1  0  0  0  0
 28 27  1  0  0  0  0
 29  7  1  0  0  0  0
 29 15  1  0  0  0  0
 29 18  1  0  0  0  0
 30 16  1  0  0  0  0
 30 17  1  0  0  0  0
 30 23  1  0  0  0  0
 30 24  1  0  0  0  0
 31 22  1  0  0  0  0
 32 24  2  0  0  0  0
 33 24  1  0  0  0  0
 34 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(CCC1(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-18-23-19-8-9-21-26(4)12-11-22(31)25(2,3)20(26)10-13-28(21,6)27(19,5)14-16-30(23,24(32)33)17-15-29(18,7)34/h8,18,20-23,31,34H,9-17H2,1-7H3,(H,32,33)

> <INCHI_KEY>
URJPXMKINYSFCX-UHFFFAOYSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.6997

> <EXACT_MASS>
472.355260024

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
55.504899644371065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,10-dihydroxy-1,2,6a,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-carboxylic acid

> <ALOGPS_LOGP>
5.69

> <JCHEM_LOGP>
5.266598184666668

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.489433291560097

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.644704013060111

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4507158302655555

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
135.3801

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.93e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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       6.600   4.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.255  -4.444   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.276  -4.444   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.599   0.586   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.600  -1.724   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.200   0.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.278   5.615   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.266   2.126   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.933   1.356   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.933  -3.264   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.068  -0.954   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.265  -0.184   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.266  -2.494   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.934  -0.954   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.601   3.666   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.267  -0.184   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.601   2.126   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.934   3.666   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.600   1.356   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.599  -2.494   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.933  -0.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.068  -2.494   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.934   2.126   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.601   0.586   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.265  -3.264   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.599  -0.954   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.600  -0.184   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.266  -0.954   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.267   4.436   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.268   1.356   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.402  -3.264   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      11.935   1.356   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      10.601  -0.954   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      10.258   5.615   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8    9   19                                                       
CONECT    9    8   21                                                       
CONECT   10   13   20                                                       
CONECT   11   12   22                                                       
CONECT   12   11   26                                                       
CONECT   13   10   28                                                       
CONECT   14   16   27                                                       
CONECT   15   17   29                                                       
CONECT   16   14   30                                                       
CONECT   17   15   30                                                       
CONECT   18    1   23   29                                                  
CONECT   19    8   23   27                                                  
CONECT   20   10   25   26                                                  
CONECT   21    9   26   28                                                  
CONECT   22   11   25   31                                                  
CONECT   23   18   19   30                                                  
CONECT   24   30   32   33                                                  
CONECT   25    2    3   20   22                                             
CONECT   26    4   12   20   21                                             
CONECT   27    5   14   19   28                                             
CONECT   28    6   13   21   27                                             
CONECT   29    7   15   18   34                                             
CONECT   30   16   17   23   24                                             
CONECT   31   22                                                            
CONECT   32   24                                                            
CONECT   33   24                                                            
CONECT   34   29                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
20b-Hydroxyursolate	Generator
20b-Hydroxyursolic acid	Generator
20beta-Hydroxyursolate	Generator
20Β-hydroxyursolate	Generator
20Β-hydroxyursolic acid	Generator
2,10-Dihydroxy-1,2,6a,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-carboxylate	Generator

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.6997 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

2,10-dihydroxy-1,2,6a,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-carboxylic acid

Traditional Name

2,10-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

58213-73-3

SMILES

CC1C2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(CCC1(C)O)C(O)=O

InChI Identifier

InChI=1S/C30H48O4/c1-18-23-19-8-9-21-26(4)12-11-22(31)25(2,3)20(26)10-13-28(21,6)27(19,5)14-16-30(23,24(32)33)17-15-29(18,7)34/h8,18,20-23,31,34H,9-17H2,1-7H3,(H,32,33)

InChI Key

URJPXMKINYSFCX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sambucus nigra	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.69	ALOGPS
logP	5.27	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-0.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	135.38 m³·mol⁻¹	ChemAxon
Polarizability	55.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035107

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013737

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73021944

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 20beta-Hydroxyursolic acid (NP0048154)

MOL for NP0048154 (20beta-Hydroxyursolic acid)

3D MOL for NP0048154 (20beta-Hydroxyursolic acid)

3D SDF for NP0048154 (20beta-Hydroxyursolic acid)

3D-SDF for NP0048154 (20beta-Hydroxyursolic acid)

PDB for NP0048154 (20beta-Hydroxyursolic acid)

3D PDB for NP0048154 (20beta-Hydroxyursolic acid)

SMILES for NP0048154 (20beta-Hydroxyursolic acid)

INCHI for NP0048154 (20beta-Hydroxyursolic acid)

Structure for NP0048154 (20beta-Hydroxyursolic acid)

3D Structure for NP0048154 (20beta-Hydroxyursolic acid)