NP-MRD: Showing NP-Card for Ursonic acid (NP0137052)

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Record Information

Version

2.0

Created at

2022-05-30 16:40:15 UTC

Updated at

2022-05-30 16:40:15 UTC

NP-MRD ID

NP0137052

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ursonic acid

Description

Ursonic acid, also known as ursonate or bipindaloside, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Ursonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ursonic acid has been detected, but not quantified in, fruits. This could make ursonic acid a potential biomarker for the consumption of these foods. Jan Scott Wilkinson of the band contributed to Tate Britain's Schwitters retrospective in 2013. The Marlborough Gallery filed suit against the Schwitters estate in 1996, after confirming Ernst Schwitters' desire to have Mr. Lloyd continue to administer the estate in his will. In April 1944 he suffered his first stroke, at the age of 56, which left him temporarily paralyzed on one side of his body. Ursonic acid is found in Ficus microcarpa, Hedyotis lawsoniae, Schefflera heptaphylla, Hymenodictyon orixense, Incarvillea arguta, Lavandula angustifolia, Morella rubra, Rauvolfia vomitoria, Scrophularia ningpoensis, Varronia multispicata and Vochysia thyrsoidea. In 1918, his art was to change dramatically as a direct consequence of Germany's economic, political, and military collapse at the end of the First World War.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241218442D          

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  Mrv0541 02241218442D          

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  6  7  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
  9 31  1  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
 12 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 28  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137052

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C2C1C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-22,24H,9-17H2,1-7H3,(H,32,33)

> <INCHI_KEY>
MUCRYNWJQNHDJH-UHFFFAOYSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.6844

> <EXACT_MASS>
454.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
54.259989405361466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-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>
6.66

> <JCHEM_LOGP>
7.145333115333335

> <ALOGPS_LOGS>
-6.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.958292730057405

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.744125421942908

> <JCHEM_PKA_STRONGEST_BASIC>
-7.4708850131332944

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
132.87569999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.16e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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      -2.668  -3.260   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.333  -4.030   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.001  -3.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.001  -1.720   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.000   5.210   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.000   3.670   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   2.900   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.360   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.000   0.590   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.000  -0.950   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.668  -1.720   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.333  -0.950   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.333  -2.490   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.333   3.670   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.668   2.900   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.668   1.360   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.333   0.590   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.001   1.360   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.333   0.590   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.333  -0.950   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.668  -1.720   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.668  -0.180   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.000  -0.950   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335  -1.720   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335  -3.260   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.670  -4.030   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.991  -5.210   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.000  -4.030   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.012  -5.210   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.335  -1.720   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.335  -0.180   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.670   0.590   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.769  -3.054   0.000  0.00  0.00           C+0
CONECT    1    2   21   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3   12   20   33                                             
CONECT    5    6                                                            
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16   31                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    4   11   13   17                                             
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    6   14   16                                                  
CONECT   16    9   15   17                                                  
CONECT   17   12   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    4   19   21                                                  
CONECT   21    1   20   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25                                                            
CONECT   27   28                                                            
CONECT   28    1   25   27   29                                             
CONECT   29   28                                                            
CONECT   30   31                                                            
CONECT   31    9   30   32                                                  
CONECT   32   31                                                            
CONECT   33    4                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Ursonate	Generator
3-oxo-12-Ursen-28-Oic acid	HMDB
3-oxo-Urs-12-en-28-Oic acid	HMDB
3-Oxours-12-en-28-Oic acid	HMDB
Bipindaloside	HMDB
1,2,6a,6b,9,9,12a-Heptamethyl-10-oxo-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

C₃₀H₄₆O₃

Average Mass

454.6844 Da

Monoisotopic Mass

454.34470 Da

IUPAC Name

1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-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

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

CAS Registry Number

Not Available

SMILES

CC1CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C2C1C)C(O)=O

InChI Identifier

InChI=1S/C30H46O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-22,24H,9-17H2,1-7H3,(H,32,33)

InChI Key

MUCRYNWJQNHDJH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ficus microcarpa	LOTUS Database	35616633
Hedyotis lawsoniae	LOTUS Database	35616633
Heptapleurum heptaphyllum	LOTUS Database	35616633
Hymenodictyon orixense	LOTUS Database	35616633
Incarvillea arguta	LOTUS Database	35616633
Lavandula angustifolia	LOTUS Database	35616633
Morella rubra	LOTUS Database	35616633
Rauvolfia vomitoria	LOTUS Database	35616633
Scrophularia ningpoensis	LOTUS Database	35616633
Varronia multispicata	LOTUS Database	35616633
Vochysia thyrsoidea	LOTUS Database	35616633

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
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.66	ALOGPS
logP	7.15	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	132.88 m³·mol⁻¹	ChemAxon
Polarizability	54.26 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

HMDB0036007

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014822

KNApSAcK ID

C00032465

Chemspider ID

13379436

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Kurt Schwitters

METLIN ID

Not Available

PubChem Compound

13893949

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Ursonic acid (NP0137052)

MOL for NP0137052 (Ursonic acid)

3D MOL for NP0137052 (Ursonic acid)

3D SDF for NP0137052 (Ursonic acid)

3D-SDF for NP0137052 (Ursonic acid)

PDB for NP0137052 (Ursonic acid)

3D PDB for NP0137052 (Ursonic acid)

SMILES for NP0137052 (Ursonic acid)

INCHI for NP0137052 (Ursonic acid)

Structure for NP0137052 (Ursonic acid)

3D Structure for NP0137052 (Ursonic acid)