NP-MRD: Showing NP-Card for 3-Epioleanolic acid (NP0137071)

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Record Information

Version

2.0

Created at

2022-05-30 16:40:49 UTC

Updated at

2022-05-30 16:40:49 UTC

NP-MRD ID

NP0137071

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Epioleanolic acid

Description

3-Epioleanolic acid, also known as 3-epioleanolate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3-Epioleanolic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3-Epioleanolic acid is found, on average, in the highest concentration within common sages. 3-Epioleanolic acid is found in Akebia trifoliata, Amphipterygium adstringens, Bergia capensis, Boschniakia rossica, Calceolaria pinifolia, Conandron ramondioides, Ekebergia capensis, Eremophila platycalyx, Eucalyptus occidentalis, Gardenia ternifolia, Lardizabala biternata, Lotus corniculatus, Mulguraea tridens, Ocimum basilicum, Olearia paniculata, Panax ginseng, Pilea pumila, Piranhea mexicana, Platycodon grandiflorus, Scutellaria discolor, Scutellaria strigillosa, Stauntonia hexaphylla and Viscum album. 3-Epioleanolic acid was first documented in 2000 (PMID: 10960904). This could make 3-epioleanolic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02241215292D          

 36 40  0  0  0  0            999 V2000
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  1  2  1  0  0  0  0
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 19 20  1  0  0  0  0
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  6 32  1  6  0  0  0
 19 33  1  6  0  0  0
  1 34  1  6  0  0  0
 24 35  1  0  0  0  0
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M  END

     RDKit          3D

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M  END

  Mrv0541 02241215292D          

 36 40  0  0  0  0            999 V2000
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    2.1247    2.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5244    2.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6878    1.2138    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -1.2253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4863   -2.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -2.4271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -2.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8449   -2.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 22  1  0  0  0  0
  1 24  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  4 17  1  0  0  0  0
  6  7  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 29  1  0  0  0  0
 12 13  1  0  0  0  0
 12 29  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 26  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 10 31  1  1  0  0  0
  6 32  1  6  0  0  0
 19 33  1  6  0  0  0
  1 34  1  6  0  0  0
 24 35  1  0  0  0  0
 24 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137071

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23+,27-,28+,29+,30-/m0/s1

> <INCHI_KEY>
MIJYXULNPSFWEK-KDQGZELNSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.7003

> <EXACT_MASS>
456.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
54.611895472859494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-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-carboxylic acid

> <ALOGPS_LOGP>
7.09

> <JCHEM_LOGP>
6.594833433333333

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.489433291560097

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.744260336518661

> <JCHEM_PKA_STRONGEST_BASIC>
-0.835123022210091

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
133.6245

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.17e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-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-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      -2.618  -2.991   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.272  -3.739   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.077  -2.991   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.077  -1.496   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.077  -0.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.272  -0.747   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.272   0.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.077   1.496   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.272   0.747   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.618   1.496   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.618   2.993   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.312   2.993   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.312   1.496   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.966   0.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.966  -0.747   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.618  -1.496   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.272  -0.747   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.272  -2.244   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.161  -2.991   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.161  -1.496   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.963  -0.747   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.618  -1.496   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.618  -0.001   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.963  -3.739   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.509   0.747   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.312  -0.001   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.312  -1.496   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.217   5.088   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.966   3.742   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.712   5.088   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       1.284   2.266   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.272  -2.287   0.000  0.00  0.00           H+0
HETATM   33  O   UNK     0      -6.508  -3.737   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      -2.618  -4.531   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0      -3.963  -5.279   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.310  -4.486   0.000  0.00  0.00           C+0
CONECT    1    2   22   24   34                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6   17                                             
CONECT    5    4                                                            
CONECT    6    4    7   22   32                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   14   31                                             
CONECT   11   10   29                                                       
CONECT   12   13   29                                                       
CONECT   13   12   14                                                       
CONECT   14   10   13   15   26                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17    4    9   16   18                                             
CONECT   18   17                                                            
CONECT   19   20   24   33                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22    1    6   21   23                                             
CONECT   23   22                                                            
CONECT   24    1   19   35   36                                             
CONECT   25   26                                                            
CONECT   26   14   25   27                                                  
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29   11   12   28   30                                             
CONECT   30   29                                                            
CONECT   31   10                                                            
CONECT   32    6                                                            
CONECT   33   19                                                            
CONECT   34    1                                                            
CONECT   35   24                                                            
CONECT   36   24                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
3-Epioleanolate	Generator
Epi-oleanolic acid	HMDB
Epi-oleanolate	HMDB
3-alpha-Hydroxyolean-12-en-28-Oate	HMDB
3-alpha-Hydroxyolean-12-en-28-Oic acid	HMDB

Chemical Formula

C₃₀H₄₈O₃

Average Mass

456.7003 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-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-carboxylic acid

Traditional Name

(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-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-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

InChI Identifier

InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23+,27-,28+,29+,30-/m0/s1

InChI Key

MIJYXULNPSFWEK-KDQGZELNSA-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
Akebia trifoliata	LOTUS Database	35616633
Amphipterygium adstringens	LOTUS Database	35616633
Bergia capensis	LOTUS Database	35616633
Boschniakia rossica	LOTUS Database	35616633
Calceolaria pinifolia	LOTUS Database	35616633
Conandron ramondioides	LOTUS Database	35616633
Ekebergia capensis	LOTUS Database	35616633
Eremophila platycalyx	LOTUS Database	35616633
Eucalyptus occidentalis	LOTUS Database	35616633
Gardenia ternifolia	LOTUS Database	35616633
Lardizabala biternata	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Mulguraea tridens	LOTUS Database	35616633
Ocimum basilicum	LOTUS Database	35616633
Olearia paniculata	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Pilea pumila	LOTUS Database	35616633
Piranhea mexicana	LOTUS Database	35616633
Platycodon grandiflorus	LOTUS Database	35616633
Scutellaria discolor	LOTUS Database	35616633
Scutellaria strigillosa	LOTUS Database	35616633
Stauntonia hexaphylla	LOTUS Database	35616633
Viscum album	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 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

triterpenoid (CHEBI:68103 )

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	7.09	ALOGPS
logP	6.59	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.62 m³·mol⁻¹	ChemAxon
Polarizability	54.61 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

HMDB0036962

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015933

KNApSAcK ID

C00029494

Chemspider ID

10043989

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11869658

PDB ID

Not Available

ChEBI ID

68103

Good Scents ID

Not Available

References

General References

Deepak M, Handa SS: Antiinflammatory activity and chemical composition of extracts of Verbena officinalis. Phytother Res. 2000 Sep;14(6):463-5. doi: 10.1002/1099-1573(200009)14:6<463::aid-ptr611>3.0.co;2-g. [PubMed:10960904 ]

Showing NP-Card for 3-Epioleanolic acid (NP0137071)

MOL for NP0137071 (3-Epioleanolic acid)

3D MOL for NP0137071 (3-Epioleanolic acid)

3D SDF for NP0137071 (3-Epioleanolic acid)

3D-SDF for NP0137071 (3-Epioleanolic acid)

PDB for NP0137071 (3-Epioleanolic acid)

3D PDB for NP0137071 (3-Epioleanolic acid)

SMILES for NP0137071 (3-Epioleanolic acid)

INCHI for NP0137071 (3-Epioleanolic acid)

Structure for NP0137071 (3-Epioleanolic acid)

3D Structure for NP0137071 (3-Epioleanolic acid)